Synthesis of (−)-cytisine using a 6-endo aza-Michael addition

Synthesis of (−)-cytisine using a 6-endo aza-Michael addition

An asymmetric synthesis of (-)-cytisine has been achieved. The piperidine C-ring was formed using a stereodivergent intramolecular 6-endo aza-Michael addition. The B-ring was established by intramolecular pyridine N-alkylation. The absolute stereochemistry was established by an Evans acyl oxazolidin...

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Bibliographic Details
Main Authors: Barát, Viktor, Csókás, Dániel, Bates, Roderick Wayland
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2019
Subjects:
Chemistry
Science::Chemistry::Organic chemistry
Stereochemistry
Online Access:https://hdl.handle.net/10356/83277
http://hdl.handle.net/10220/50076
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Institution: Nanyang Technological University
Language: English
Description
Summary:An asymmetric synthesis of (-)-cytisine has been achieved. The piperidine C-ring was formed using a stereodivergent intramolecular 6-endo aza-Michael addition. The B-ring was established by intramolecular pyridine N-alkylation. The absolute stereochemistry was established by an Evans acyl oxazolidinone enolate alkylation reaction that proceeded with an unexpected stereochemical outcome due to participation of the pyridine nitrogen lone pair.

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